N ‐(4‐(4‐(2‐Halogenophenyl)piperazin‐1‐yl)butyl) Substituted Cinnamoyl Amide Derivatives as Dopamine D 2 and D 3 Receptor Ligands
A series of eight substituted N ‐(4‐(4‐(2‐halogenophenyl)piperazin‐1‐yl)butyl)‐3‐phenylacryl amide derivatives have been synthesized and screened for binding affinities at dopamine hD 2 and hD 3 receptors. All compounds have shown high to remarkable receptor affinities and some have led to distinct...
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| Veröffentlicht in: | Archiv der Pharmazie (Weinheim) 2007-04, Vol.340 (4), p.178-184 |
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| container_title | Archiv der Pharmazie (Weinheim) |
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| creator | Saur, Oliver Hackling, Anneke E. Perachon, Sylvie Schwartz, Jean‐Charles Sokoloff, Pierre Stark, Holger |
| description | A series of eight substituted
N
‐(4‐(4‐(2‐halogenophenyl)piperazin‐1‐yl)butyl)‐3‐phenylacryl amide derivatives have been synthesized and screened for binding affinities at dopamine hD
2
and hD
3
receptors. All compounds have shown high to remarkable receptor affinities and some have led to distinct selectivity for D
3
receptors. Highest D
3
‐receptor affinity has been observed for 3‐(4‐aminophenyl)‐
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)acryl amide (hD
3
K
i
0.9 nM; hD
2
K
i
17.4 nM). Selectivity ratio has been best for 3‐(4‐chlorophenyl)‐
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)acryl amide with a 56‐fold preference for hD
3
versus hD
2
. A functional activity test has been performed by a mitogenesis test for
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)‐3,3‐diphenylacryl amide, which, surprisingly, has shown full agonist properties. |
| doi_str_mv | 10.1002/ardp.200600196 |
| format | Article |
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N
‐(4‐(4‐(2‐halogenophenyl)piperazin‐1‐yl)butyl)‐3‐phenylacryl amide derivatives have been synthesized and screened for binding affinities at dopamine hD
2
and hD
3
receptors. All compounds have shown high to remarkable receptor affinities and some have led to distinct selectivity for D
3
receptors. Highest D
3
‐receptor affinity has been observed for 3‐(4‐aminophenyl)‐
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)acryl amide (hD
3
K
i
0.9 nM; hD
2
K
i
17.4 nM). Selectivity ratio has been best for 3‐(4‐chlorophenyl)‐
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)acryl amide with a 56‐fold preference for hD
3
versus hD
2
. A functional activity test has been performed by a mitogenesis test for
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)‐3,3‐diphenylacryl amide, which, surprisingly, has shown full agonist properties.</description><identifier>ISSN: 0365-6233</identifier><identifier>EISSN: 1521-4184</identifier><identifier>DOI: 10.1002/ardp.200600196</identifier><language>eng</language><ispartof>Archiv der Pharmazie (Weinheim), 2007-04, Vol.340 (4), p.178-184</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c169t-be5ae6ea2ca14b4937309a8eac964837f213f335fcc1cadff7b35cdc170e55573</citedby><cites>FETCH-LOGICAL-c169t-be5ae6ea2ca14b4937309a8eac964837f213f335fcc1cadff7b35cdc170e55573</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Saur, Oliver</creatorcontrib><creatorcontrib>Hackling, Anneke E.</creatorcontrib><creatorcontrib>Perachon, Sylvie</creatorcontrib><creatorcontrib>Schwartz, Jean‐Charles</creatorcontrib><creatorcontrib>Sokoloff, Pierre</creatorcontrib><creatorcontrib>Stark, Holger</creatorcontrib><title>N ‐(4‐(4‐(2‐Halogenophenyl)piperazin‐1‐yl)butyl) Substituted Cinnamoyl Amide Derivatives as Dopamine D 2 and D 3 Receptor Ligands</title><title>Archiv der Pharmazie (Weinheim)</title><description>A series of eight substituted
N
‐(4‐(4‐(2‐halogenophenyl)piperazin‐1‐yl)butyl)‐3‐phenylacryl amide derivatives have been synthesized and screened for binding affinities at dopamine hD
2
and hD
3
receptors. All compounds have shown high to remarkable receptor affinities and some have led to distinct selectivity for D
3
receptors. Highest D
3
‐receptor affinity has been observed for 3‐(4‐aminophenyl)‐
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)acryl amide (hD
3
K
i
0.9 nM; hD
2
K
i
17.4 nM). Selectivity ratio has been best for 3‐(4‐chlorophenyl)‐
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)acryl amide with a 56‐fold preference for hD
3
versus hD
2
. A functional activity test has been performed by a mitogenesis test for
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)‐3,3‐diphenylacryl amide, which, surprisingly, has shown full agonist properties.</description><issn>0365-6233</issn><issn>1521-4184</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNo9kM1KAzEUhYMoWKtb11nqYupNMpnpLEurVigK_qyHO5k7NTJ_JFOhrnwBwWf0SUxRurjfge_AXRzGzgVMBIC8Qlf2EwmQAIgsOWAjoaWIYjGND9kIVKKjRCp1zE68fwMABVKP2Nc9__n8voj3kAFLrLs1tV3_Su22vuxtTw4_bBsqES6oYjME8qdN4Qc7bAYq-dy2LTbdtuazxpbEF-TsOw72nTxHzxddj41tg-eSY1uGVPyRDPVD5_jKroPzp-yowtrT2X-O2cvN9fN8Ga0ebu_ms1VkRJINUUEaKSGUBkVcxJlKFWQ4JTRZEk9VWkmhKqV0ZYwwWFZVWihtSiNSIK11qsZs8vfXuM57R1XeO9ug2-YC8t2Y-W7MfD-m-gVCLW5u</recordid><startdate>200704</startdate><enddate>200704</enddate><creator>Saur, Oliver</creator><creator>Hackling, Anneke E.</creator><creator>Perachon, Sylvie</creator><creator>Schwartz, Jean‐Charles</creator><creator>Sokoloff, Pierre</creator><creator>Stark, Holger</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200704</creationdate><title>N ‐(4‐(4‐(2‐Halogenophenyl)piperazin‐1‐yl)butyl) Substituted Cinnamoyl Amide Derivatives as Dopamine D 2 and D 3 Receptor Ligands</title><author>Saur, Oliver ; Hackling, Anneke E. ; Perachon, Sylvie ; Schwartz, Jean‐Charles ; Sokoloff, Pierre ; Stark, Holger</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c169t-be5ae6ea2ca14b4937309a8eac964837f213f335fcc1cadff7b35cdc170e55573</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Saur, Oliver</creatorcontrib><creatorcontrib>Hackling, Anneke E.</creatorcontrib><creatorcontrib>Perachon, Sylvie</creatorcontrib><creatorcontrib>Schwartz, Jean‐Charles</creatorcontrib><creatorcontrib>Sokoloff, Pierre</creatorcontrib><creatorcontrib>Stark, Holger</creatorcontrib><collection>CrossRef</collection><jtitle>Archiv der Pharmazie (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Saur, Oliver</au><au>Hackling, Anneke E.</au><au>Perachon, Sylvie</au><au>Schwartz, Jean‐Charles</au><au>Sokoloff, Pierre</au><au>Stark, Holger</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N ‐(4‐(4‐(2‐Halogenophenyl)piperazin‐1‐yl)butyl) Substituted Cinnamoyl Amide Derivatives as Dopamine D 2 and D 3 Receptor Ligands</atitle><jtitle>Archiv der Pharmazie (Weinheim)</jtitle><date>2007-04</date><risdate>2007</risdate><volume>340</volume><issue>4</issue><spage>178</spage><epage>184</epage><pages>178-184</pages><issn>0365-6233</issn><eissn>1521-4184</eissn><abstract>A series of eight substituted
N
‐(4‐(4‐(2‐halogenophenyl)piperazin‐1‐yl)butyl)‐3‐phenylacryl amide derivatives have been synthesized and screened for binding affinities at dopamine hD
2
and hD
3
receptors. All compounds have shown high to remarkable receptor affinities and some have led to distinct selectivity for D
3
receptors. Highest D
3
‐receptor affinity has been observed for 3‐(4‐aminophenyl)‐
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)acryl amide (hD
3
K
i
0.9 nM; hD
2
K
i
17.4 nM). Selectivity ratio has been best for 3‐(4‐chlorophenyl)‐
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)acryl amide with a 56‐fold preference for hD
3
versus hD
2
. A functional activity test has been performed by a mitogenesis test for
N
‐(4‐(4‐(2‐fluorophenyl)piperazin‐1‐yl)butyl)‐3,3‐diphenylacryl amide, which, surprisingly, has shown full agonist properties.</abstract><doi>10.1002/ardp.200600196</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0365-6233 |
| ispartof | Archiv der Pharmazie (Weinheim), 2007-04, Vol.340 (4), p.178-184 |
| issn | 0365-6233 1521-4184 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ardp_200600196 |
| source | Wiley-Blackwell Journals |
| title | N ‐(4‐(4‐(2‐Halogenophenyl)piperazin‐1‐yl)butyl) Substituted Cinnamoyl Amide Derivatives as Dopamine D 2 and D 3 Receptor Ligands |
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